I Wore a Bathrobe to a Billionaire’s Home

Storytime…

I was slurping oysters in the backyard of what I had to guess is one of the nicest homes I’ve set foot in. To my right, the Salish Sea in Victoria, BC. The weather was perfect, a brisk 65 degrees. I was exchanging small talk with the man who just finished putting on one of the best “conferences” I’ve been to, which he designed to be an “anti-conference.”

This conference was called IP2. Short for Interesting People 2, the second iteration of Andrew Wilkinson’s “anti-conference.” Where he individually selects attendees that are some of the most interesting people he knows.

2 month’s prior I saw an email drop in my inbox from Andrew that he was hosting this conference for interesting people, he invited me to apply. I assumed I was probably on an email list of his twitter subscribers of and that he pushed this out to. The speakers included founders and entrepreneurs in the space that I looked up to: Shaan Puri, Patrick Campbell, Steph Smith, Chris Sparling, Cody Sanchez, and Nick Gray.

It had a big price tag. It cost $6,000. I had to pay up front too, I would get refunded only if I didn’t get accepted... I wasn’t sure if I should do this. That’s a lot of money that I knew I would have to pay for myself, out of pocket. Work would not pay for this. I told myself I wasn’t going to travel for a bit while I figure out my next play in SF. I recalled back to a post I wrote weeks back about pay for access. I believe that I need to put myself in the rooms I didn’t deserve to be in, with the people ahead of me. Eventually, I’ll become one of those people. This was my chance to meet more of those people. I honestly didn’t think I was going to get in.

Surprise. I got in. I was excited and anxious. Oh shit, now I need to liquidate from my stock portfolio to pay this six grand charge on my credit card. I was in.

Fast forward to the day before the conference. I get to my hotel and open up the pamphlet they made intro-ing all the speaker and attendees. Holy shit. More rock star founders. Greg Isenberg, Sam Corcos, Ayman Al-Abdulla, Matthew Dicks, people running 100 million dollar businesses. Some even running billion dollar businesses. Then there’s me: Jared, Product Manager from Dexcom. I had no idea how I got into this group.

I set my expectations coming into this. I’m was not coming to look for a job nor a new business idea. I’m coming to meet all these interesting people that were ahead of me. Understand the problems they have in their businesses, ask questions, and learn how these people think. I was there to learn.

The conference was run by Nick Gray. He wrote the 2-hour cocktail party, a book that changed my life. I was blown away by how good he was at this, he put on a clinic. It came naturally. There was a pre-party the night before, multiple breakout sessions, fireside chats, activities around Victoria, and tea time. To be clear, Andrew also had a full team in the background that put a ton of this together for weeks leading up to this. They deserve a ton of credit for how well this went too.

I had imposter syndrome the first day. 90% of the people there were founders. I was trying figure out how to share my story, how could I sound interesting? I was just a product manager at a CGM company. But that WAS my thing. I was a product manager at Dexcom, a company that build’s one of the most popular CGMs in the world. All these people we’re all great business builders. Health got them really excited. I knew health. They dug into my story, all the business projects I started, my media company, my DJ career, my biomechanics research, my preventative health project, how I stay healthy. That’s when I realized. I’m not so different from these people. The one difference is that they just got a head start on building a business. They already started. I knew I’d be there soon.

I have pages and pages of notes and nuggets that I got from this conference. I’ll save that for a different time…

Let’s get back to the slurping of oysters.

This was the final party of the event. Nick warned us in the group chat that it was going to get cold at night, and to bring a jacket. He said to bring something warm if we didn’t have a jacket, such as the bathrobe from our hotel room (we were staying at the Fairmont). Someone in the group chat for the conference shared a picture of themselves in their bath robe saying the fit went hard. Honestly it kinda did. I wanted to be part of this bit. I threw my bathrobe over my outfit and rushed down the elevator to get on the bus.

I walk in the lobby, everyone is there, we’re heading onto the bus in two minutes. Everyone looks… nice. No bathrobes on. The one guy who posted the photo in the bathrobe wasn’t wearing his bathrobe. I was the only one! I stuck out like a sore thumb. I thought this was a bit. Everyone looked at me and laughed, they loved it. “You actually wore the bathrobe?!?” I said hell yeah, I thought it would be funny, and that other people were wearing theirs too. Nope. Just me.

This was my chance. I could have thrown the bathrobe into the back of the bus and got it later on the way home, or I could stand out and be remembered. I went with option two. I also got a burst of confidence when Shaan told me “nah man it looks good, now you’re committed, you gotta see it through.” I saw it through.

There I am, slurping oysters with Andrew Wilkinson, the owner of a multi million dollar company. The organizer of this conference. He’s wearing a patterned white bottom down t-shirt. Could be designer. Not sure. There I am. wearing a bathrobe.

I said “Hey look we’re matching.”

His response? “Yeah nice jacket!!”

Then I broke it to him. This was the bathrobe from the Fairmont hotel. He told me he legitimately thought I was just wearing a patterned oversized jacket. Only in this space could that pass for fashion.

That’s when I realized I had an opportunity. I could leave an impression with every single person at the event. For the past two days I was making friends, being curious, learning, and connecting with successful people. I convinced people I was a normal(ish) guy. By doing this they weren’t going to forget who I was.

Next time I reach out to connect with an attendee from IP2, they’re going to recall exactly who I was. I was the guy who wore a bathrobe around the entire night. Even to a nightclub after.

I was the guy who wore a bathrobe to a billionaire’s house party.

Why am I sharing this with you? It’s not just a funny story. It’s a lesson you can apply anywhere.

If you want to stand out and be remembered you need to find a way to make people remember you. They need to know you for something. So go do something a little different.

What’s the worst that can happen? You won’t die.

Have some fun with it.

Love Ya,

Jared

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